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474790

Sigma-Aldrich

MG-132

A cell-permeable, potent, reversible proteasome inhibitor (Ki = 4 nM).

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Synonym(s):
Z-Leu-Leu-Leu-al, Carbobenzoxy-L-leucyl-L-leucyl-L-leucinal, Z-LLL-CHO, Proteasome Inhibitor XI, MG-132
Empirical Formula (Hill Notation):
C26H41N3O5
CAS Number:
133407-82-6
Molecular Weight:
475.62
MDL number:
MFCD00674886
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze

color

white

solubility

DMSO: 20 mg/mL
ethanol: 20 mg/mL

shipped in

ambient

storage temp.

−20°C

SMILES string

[H]C(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)OCc1ccccc1

InChI

1S/C26H41N3O5/c1-17(2)12-21(15-30)27-24(31)22(13-18(3)4)28-25(32)23(14-19(5)6)29-26(33)34-16-20-10-8-7-9-11-20/h7-11,15,17-19,21-23H,12-14,16H2,1-6H3,(H,27,31)(H,28,32)(H,29,33)/t21-,22-,23-/m0/s1

InChI key

TZYWCYJVHRLUCT-VABKMULXSA-N

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Amino Acid Sequence

Z-Leu-Leu-Leu-al

General description

A potent, reversible, and cell-permeable proteasome inhibitor (Ki = 4 nM). Reduces the degradation of ubiquitin-conjugated proteins in mammalian cells and permeable strains of yeast by the 26S complex without affecting its ATPase or isopeptidase activities. Activates c-Jun N-terminal kinase (JNK1), which initiates apoptosis. Inhibits NF-κB activation (IC50 = 3 µM). Also reported to increases the survival rate of mesenchymal stem cells following their transplantation. Prevents β-secretase cleavage. A 10 mM (1 mg/210 µl) solution of MG-132 (Cat. No. 474791) in DMSO is also available. This material is ≥98% pure by HPLC. A material with ≥95% purity by HPLC (Cat. No. 474787) is also available.
Potent, reversible, and cell-permeable proteasome inhibitor (Ki = 4 nM). Reduces the degradation of ubiquitin-conjugated proteins in mammalian cells and permeable stains of yeast by the 26S complex without affecting its ATPase or isopeptidase activities. Activates c-Jun N-terminal kinase (JNK1) which initiates apoptosis. Inhibits NF-kB activation (IC50 = 3 µM). Also reported to increases the survival rate of mesenchymal stem cells following their transplantation.

Biochem/physiol Actions

Cell permeable: yes
Primary Target
proteasome
Product does not compete with ATP.
Reversible: yes
Target IC50: 3 µM against NF-κB activation
Target Ki: 4 nM against proteasome

Warning

Toxicity: Standard Handling (A)

Sequence

Z-Leu-Leu-Leu-CHO

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 1 month at -20°C.

Other Notes

Li, Z.W. et al. 2011. Sheng Li Xue Bao. 63, 525.
Steinhilb, M.L., et al. 2001. J. Biol. Chem.276, 4476.
Meriin, A.B., et al. 1998. J. Biol. Chem. 273, 6373.
Adams, J., and Stein, R. 1996. Ann. Rep. Med. Chem.31, 279.
Klafki, H.W., et al. 1996. J. Biol. Chem.271, 2865.
Lee, D.H., and Goldberg, A.L., 1996. J. Biol. Chem.271, 27280.
Wiertz, E.J., et al. 1996. Cell84, 769.
Jensen, T.J., et al. 1995. Cell 83, 129.
Read, M.A., et al. 1995. Immunity2, 493.
Rock, K.L., et al. 1994. Cell 78, 761.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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Cross-species pathway transplantation enables insight into a biological process not possible through traditional approaches. We replaced the enzymes catalyzing the entire Saccharomyces cerevisiae adenine de novo biosynthesis pathway with the human pathway. While the 'humanized' yeast grew in the absence
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Nonalcoholic fatty liver disease (NAFLD) and nonalcoholic steatohepatitis (NASH) are emerging as leading causes of liver disease worldwide and have been recognized as one of the major unmet medical needs of the 21st century. Our recent translational studies in mouse
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